HUT74621A - New hydroxylamine derivatives and pharmaceutical compositions containing them - Google Patents

New hydroxylamine derivatives and pharmaceutical compositions containing them

Info

Publication number
HUT74621A
HUT74621A HU9501756A HU9501756A HUT74621A HU T74621 A HUT74621 A HU T74621A HU 9501756 A HU9501756 A HU 9501756A HU 9501756 A HU9501756 A HU 9501756A HU T74621 A HUT74621 A HU T74621A
Authority
HU
Hungary
Prior art keywords
alkyl
pct
formula
group
compounds
Prior art date
Application number
HU9501756A
Other languages
Hungarian (hu)
Other versions
HU218480B (en
HU9501756D0 (en
Inventor
Ede Marvanyos
Laszlo Ueroegi
Katalin Biro
Laszlo Jaszlits
Andrea Jednakovits
Mihaly Barabas
Dr Hegedues Erzsebet Radvanyne
Maria Kuerthy
Nagy Istvanne Udvardy
Original Assignee
Biorex Kutato Fejlesztoe Kft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Biorex Kutato Fejlesztoe Kft filed Critical Biorex Kutato Fejlesztoe Kft
Priority to HU9501756A priority Critical patent/HU218480B/en
Publication of HU9501756D0 publication Critical patent/HU9501756D0/en
Priority to HR960279A priority patent/HRP960279B1/en
Priority to IN1286DE1996 priority patent/IN185781B/en
Priority to ZA9604978A priority patent/ZA964978B/en
Priority to PT96921009T priority patent/PT832079E/en
Priority to EP96921009A priority patent/EP0832079B1/en
Priority to AT96921009T priority patent/ATE215075T1/en
Priority to PL96324197A priority patent/PL185592B1/en
Priority to SK1713-97A priority patent/SK282953B6/en
Priority to CZ19974015A priority patent/CZ295547B6/en
Priority to KR1019970709431A priority patent/KR100444780B1/en
Priority to US08/914,115 priority patent/US6002002A/en
Priority to SI9630462T priority patent/SI0832079T1/en
Priority to CA002221689A priority patent/CA2221689C/en
Priority to DK96921009T priority patent/DK0832079T3/en
Priority to ES96921009T priority patent/ES2174077T3/en
Priority to IL12214196A priority patent/IL122141A/en
Priority to AU62376/96A priority patent/AU703163B2/en
Priority to JP50282997A priority patent/JP4083800B2/en
Priority to YU36996A priority patent/YU49419B/en
Priority to DE69620175T priority patent/DE69620175T2/en
Priority to PCT/HU1996/000033 priority patent/WO1997000251A1/en
Priority to BR9608929A priority patent/BR9608929A/en
Publication of HUT74621A publication Critical patent/HUT74621A/en
Priority to MXPA/A/1997/010172A priority patent/MXPA97010172A/en
Publication of HU218480B publication Critical patent/HU218480B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Epidemiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyridine Compounds (AREA)

Abstract

PCT No. PCT/HU96/00033 Sec. 371 Date May 13, 1998 Sec. 102(e) Date May 13, 1998 PCT Filed Jun. 14, 1996 PCT Pub. No. WO97/00251 PCT Pub. Date Jan. 3, 1997The present invention provides novel hydroxylamine derivatives represented by the general formula: wherein: X is O, -NH, or a group of formula NR', wherein R and R' are independently selected from alkyl, cycloalkyl, phenylalkyl, phenyl optionally substituted with halo, haloalkyl, alkyl, alkoxy or nitro; and a N-containing heterocyclic ring; R1 is H or alkanoyl, R2 is H or hydroxy optionally acylated with alkanoyl, and R3 is a group of the formula -NR4R5 wherein R4 and R5 are independently selected from H, alkyl, and a group of the formula -CO-NH-R wherein R is as defined above, or wherein R4 and R5 when taken together form a 5- to 7-membered heterocyclic ring which may optionally contain one additional hetero atom selected from nitrogen, oxygen and sulfur and which is optionally substituted with alkyl or phenylalkyl. Also provided are pharmaceutically acceptable acid addition salts of the compounds defined above, as well as pharmaceutical compositions containing the compounds or their acid addition salts as active ingredients. The compounds of the invention have been shown to have anti-ischemic effects.
HU9501756A 1995-06-15 1995-06-15 Hydroxylamine derivatives, process for producing them and pharmaceutical compositions containing them HU218480B (en)

Priority Applications (24)

Application Number Priority Date Filing Date Title
HU9501756A HU218480B (en) 1995-06-15 1995-06-15 Hydroxylamine derivatives, process for producing them and pharmaceutical compositions containing them
HR960279A HRP960279B1 (en) 1995-06-15 1996-06-12 Hydroxylamine derivatives and pharmaceutical compositions
IN1286DE1996 IN185781B (en) 1995-06-15 1996-06-12
ZA9604978A ZA964978B (en) 1995-06-15 1996-06-12 Hydroxylamine derivatives and pharmaceutical cmposition.
BR9608929A BR9608929A (en) 1995-06-15 1996-06-14 Anti-ischemic hydroxylamine derivatives and pharmaceutical compositions
SI9630462T SI0832079T1 (en) 1995-06-15 1996-06-14 Anti-ischaemic hydroxylamine derivatives and pharmaceutical compositions
ES96921009T ES2174077T3 (en) 1995-06-15 1996-06-14 ANTI-CHEMICAL HYDROXYLAMINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS.
AT96921009T ATE215075T1 (en) 1995-06-15 1996-06-14 HYDROXYLAMINE DERIVATIVES HAVING ANTI-ISCHEMIC EFFECT AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
PL96324197A PL185592B1 (en) 1995-06-15 1996-06-14 Derivatives of hydroxylamine and pharmaceutic agents against ischaemia
SK1713-97A SK282953B6 (en) 1995-06-15 1996-06-14 Anti-ischaemic hydroxylamine derivatives and pharmaceutical compositions
CZ19974015A CZ295547B6 (en) 1995-06-15 1996-06-14 Hydroxylamine derivatives, process of their preparation and their use
KR1019970709431A KR100444780B1 (en) 1995-06-15 1996-06-14 Anti-ischemic hydroxylamine derivatives and pharmaceutical compositions
US08/914,115 US6002002A (en) 1995-06-15 1996-06-14 Anti-ischaemic hydroxylamine derivatives and pharmaceutical compositions
PT96921009T PT832079E (en) 1995-06-15 1996-06-14 ANTI-ISCHEMIC HYDROXYLAMINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS
CA002221689A CA2221689C (en) 1995-06-15 1996-06-14 Anti-ischaemic hydroxylamine derivatives and pharmaceutical compositions
DK96921009T DK0832079T3 (en) 1995-06-15 1996-06-14 Anti-ischemic hydroxylamine derivatives and pharmaceutical compositions
EP96921009A EP0832079B1 (en) 1995-06-15 1996-06-14 Anti-ischaemic hydroxylamine derivatives and pharmaceutical compositions
IL12214196A IL122141A (en) 1995-06-15 1996-06-14 Hydroxylamine derivatives, their preparation and pharmaceutical compositions containing them
AU62376/96A AU703163B2 (en) 1995-06-15 1996-06-14 Anti-ischaemic hydroxylamine derivatives and pharmaceutical compositions
JP50282997A JP4083800B2 (en) 1995-06-15 1996-06-14 Anti-ischemic hydroxylamine derivatives and pharmaceutical compositions
YU36996A YU49419B (en) 1995-06-15 1996-06-14 Novel hidroxylamine derivatives and pharmaceutical compositions
DE69620175T DE69620175T2 (en) 1995-06-15 1996-06-14 HYDROXYLAMINE DERIVATIVES WITH ANTI-ISCHEMIC EFFECT AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
PCT/HU1996/000033 WO1997000251A1 (en) 1995-06-15 1996-06-14 Anti-ischaemic hydroxylamine derivatives and pharmaceutical compositions
MXPA/A/1997/010172A MXPA97010172A (en) 1995-06-15 1997-12-15 Derivatives of anti-ischemic hydroxylamine and pharmaceutical compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU9501756A HU218480B (en) 1995-06-15 1995-06-15 Hydroxylamine derivatives, process for producing them and pharmaceutical compositions containing them

Publications (3)

Publication Number Publication Date
HU9501756D0 HU9501756D0 (en) 1995-08-28
HUT74621A true HUT74621A (en) 1997-01-28
HU218480B HU218480B (en) 2000-09-28

Family

ID=10986948

Family Applications (1)

Application Number Title Priority Date Filing Date
HU9501756A HU218480B (en) 1995-06-15 1995-06-15 Hydroxylamine derivatives, process for producing them and pharmaceutical compositions containing them

Country Status (23)

Country Link
US (1) US6002002A (en)
EP (1) EP0832079B1 (en)
JP (1) JP4083800B2 (en)
KR (1) KR100444780B1 (en)
AT (1) ATE215075T1 (en)
AU (1) AU703163B2 (en)
BR (1) BR9608929A (en)
CA (1) CA2221689C (en)
CZ (1) CZ295547B6 (en)
DE (1) DE69620175T2 (en)
DK (1) DK0832079T3 (en)
ES (1) ES2174077T3 (en)
HR (1) HRP960279B1 (en)
HU (1) HU218480B (en)
IL (1) IL122141A (en)
IN (1) IN185781B (en)
PL (1) PL185592B1 (en)
PT (1) PT832079E (en)
SI (1) SI0832079T1 (en)
SK (1) SK282953B6 (en)
WO (1) WO1997000251A1 (en)
YU (1) YU49419B (en)
ZA (1) ZA964978B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA64716C2 (en) * 1996-08-09 2004-03-15 Pharmaceuticals for therapy or prevention of illnesses connected with dysfunction of vascular endothelial cells
PL365909A1 (en) * 2000-02-21 2005-01-10 Astrazeneca Ab Piperidine- and piperazine substituted n-hydroxyformamides as inhibitors of metalloproteinases
WO2003057664A1 (en) 2002-01-11 2003-07-17 Biorex Kutató És Fejlesztö Rt. Carboxamidine derivatives and their use in the treatment of vascular diseases
JP2007526912A (en) 2004-01-30 2007-09-20 グレート・レークス・ケミカル・コーポレーション Manufacturing method and system, composition, surfactant, monomer unit, metal complex, phosphate ester, glycol, aqueous film-forming foam, and foam stabilizer
US8318656B2 (en) 2007-07-03 2012-11-27 E. I. Du Pont De Nemours And Company Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers
KR101405103B1 (en) * 2014-03-25 2014-06-10 재 남 우 Equipment opening and shutting of superhigh pressure compressed gas with manual opening device on lever-age

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE369944C (en) * 1918-03-07 1923-02-24 Anilin Fabrikation Ag Process for the preparation of tetrahydronaphthalene
DE2651083A1 (en) * 1976-11-09 1978-05-18 Hoechst Ag NEW O-ALKYLATED HYDROXYLAMINE, METHOD FOR THEIR PRODUCTION AND THEIR USE
EP0369944A1 (en) * 1988-11-18 1990-05-23 Ciba-Geigy Ag Substituted oxadiamino butanes
EP0495750A3 (en) * 1991-01-14 1992-09-16 Ciba-Geigy Ag Heterocyclic hydroxylamine

Also Published As

Publication number Publication date
JPH11507662A (en) 1999-07-06
HRP960279A2 (en) 1997-12-31
SI0832079T1 (en) 2002-08-31
DE69620175D1 (en) 2002-05-02
JP4083800B2 (en) 2008-04-30
BR9608929A (en) 1999-06-15
CA2221689A1 (en) 1997-01-03
YU36996A (en) 1998-11-05
IN185781B (en) 2001-04-28
SK282953B6 (en) 2003-01-09
PT832079E (en) 2002-07-31
ATE215075T1 (en) 2002-04-15
ZA964978B (en) 1997-02-24
DK0832079T3 (en) 2002-06-03
MX9710172A (en) 1998-07-31
DE69620175T2 (en) 2002-08-22
HRP960279B1 (en) 2002-02-28
CZ401597A3 (en) 1998-04-15
IL122141A0 (en) 1998-04-05
AU6237696A (en) 1997-01-15
PL185592B1 (en) 2003-06-30
CA2221689C (en) 2007-08-07
KR19990022961A (en) 1999-03-25
EP0832079B1 (en) 2002-03-27
KR100444780B1 (en) 2004-11-26
SK171397A3 (en) 1998-06-03
AU703163B2 (en) 1999-03-18
US6002002A (en) 1999-12-14
ES2174077T3 (en) 2002-11-01
IL122141A (en) 2003-07-06
YU49419B (en) 2006-01-16
PL324197A1 (en) 1998-05-11
CZ295547B6 (en) 2005-08-17
WO1997000251A1 (en) 1997-01-03
HU218480B (en) 2000-09-28
EP0832079A1 (en) 1998-04-01
HU9501756D0 (en) 1995-08-28

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Legal Events

Date Code Title Description
GB9A Succession in title

Owner name: CYTRX CORPORATION, US

Free format text: FORMER OWNER(S): BIOREX KUTATO ES FEJLESZTOE RT., HU

MM4A Lapse of definitive patent protection due to non-payment of fees